2-Methyl-2-butanol → Dasabuvir

HRID 58411

反応式

HRID 58411 の反応式
C(P(C(C)(C)C)C1C(OC)=CC=C(OC)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)(CC)(C)C.CS(O[C:54]1[CH:63]=[CH:62][C:61]2[C:56](=[CH:57][CH:58]=[C:59]([C:64]3[CH:69]=[C:68]([N:70]4[CH:75]=[CH:74][C:73](=[O:76])[NH:72][C:71]4=[O:77])[CH:67]=[C:66]([C:78]([CH3:81])([CH3:80])[CH3:79])[C:65]=3[O:82][CH3:83])[CH:60]=2)[CH:55]=1)(=O)=O.[CH3:84][S:85]([NH2:88])(=[O:87])=[O:86]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:78]([C:66]1[C:65]([O:82][CH3:83])=[C:64]([C:59]2[CH:60]=[C:61]3[C:56](=[CH:57][CH:58]=2)[CH:55]=[C:54]([NH:88][S:85]([CH3:84])(=[O:87])=[O:86])[CH:63]=[CH:62]3)[CH:69]=[C:68]([N:70]2[CH:75]=[CH:74][C:73](=[O:76])[NH:72][C:71]2=[O:77])[CH:67]=1)([CH3:81])([CH3:80])[CH3:79]

参加物

7

反応物 5

HCID 64052-Methyl-2-butanol2 回HCID 62657Potassium Phosphate, TribasicHCID 72879MethanesulfonamideHCID 44233348Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-(1,1'-biphenyl)-2-yl)phosphineHCID 866938706-(3-tert-Butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl methanesulfonate

生成物 1

HCID 56640146Dasabuvir

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
80 °C

実験手順

Tris(dibenzylideneacetone)dipalladium(0) (0.0037 g, 4.04 μmol), di-tert-butyl(2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (0.0047 g, 9.7 μmol) and milled potassium phosphate tribasic (0.094 g, 0.445 mmol) were charged to a 40-mL reaction vial inside an inert atmosphere glove box. tert-Amyl alcohol (1.0 mL) was added, the contents were heated to 80° C. and stirred at this temperature for 30 minutes. The reaction mixture was cooled down to room temperature. 6-(3-tert-Butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl methanesulfonate (0.2 g, 0.404 mmol), methanesulfonamide (0.046 g, 0.485 mmol) and tert-amyl alcohol (1.5 mL) were added to a 40-mL reaction vial. The reaction temperature was raised to 110° C., and the contents were stirred for 14 hours. HPLC analysis of the reaction mixture showed that the titled compound was formed in 7 area % at 210 nm.

後処理

  1. additionwere charged to a 40-mL reaction vial inside an inert atmosphere glove box
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. temperatureThe reaction temperature was raised to 110° C.
  4. stirringthe contents were stirred for 14 hours

出典と根拠

ORDレコード
ord-9b8c776c0edb4ccf8a80a3b98fed346f
出典データセット
uspto-grants-2016_09
特許番号
US09434698B2

関連ノート

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